Benzoyl chloride → Ethyl 5-benzamido-1-methyl-2-indolecarboxylate

HRID 565025Notes

Reaction equation

HRID 565025 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]2.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:17]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]2)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 11424506Ethyl 5-amino-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 21194638Ethyl 5-benzamido-1-methyl-2-indolecarboxylateYield 52.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 20 ml of pyridine was dissolved 0.80 g (3.67 mmol) of ethyl 5-amino-1-methyl-2-indolecarboxylate. While stirring at room temperature, 0.57 g (4.03 mmol) of benzoyl chloride was added to the solution. After stirring for 2 hours at 70° C., the reaction mixture was cooled to room temperature and then poured onto ice water. The mixture was then extracted three times with ethyl acetate. The combined extracts were washed with 1N hydrochloric acid and then with saturated sodium hydrogencarbonate solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 0.62 g (52.5%) of ethyl 5-benzamido-1-methyl-2-indolecarboxylate.

Workup

  1. stirringAfter stirring for 2 hours at 70° C.
  2. temperaturethe reaction mixture was cooled to room temperature
  3. additionpoured onto ice water
  4. extractionThe mixture was then extracted three times with ethyl acetate
  5. washThe combined extracts were washed with 1N hydrochloric acid
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-517961414f3a491c952c808e48a6e1b8
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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